MXPA05010288A - Derivados de bencenosulfonamida, metodo para su produccion y uso de los mismos para el tratamiento del dolor. - Google Patents
Derivados de bencenosulfonamida, metodo para su produccion y uso de los mismos para el tratamiento del dolor.Info
- Publication number
- MXPA05010288A MXPA05010288A MXPA05010288A MXPA05010288A MXPA05010288A MX PA05010288 A MXPA05010288 A MX PA05010288A MX PA05010288 A MXPA05010288 A MX PA05010288A MX PA05010288 A MXPA05010288 A MX PA05010288A MX PA05010288 A MXPA05010288 A MX PA05010288A
- Authority
- MX
- Mexico
- Prior art keywords
- preparation
- yield
- group
- formula
- acid
- Prior art date
Links
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 208000002193 Pain Diseases 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 349
- 238000000034 method Methods 0.000 claims abstract description 73
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 206
- 150000001875 compounds Chemical class 0.000 claims description 195
- 239000000203 mixture Substances 0.000 claims description 84
- 239000002253 acid Substances 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 239000012190 activator Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 382
- 238000005481 NMR spectroscopy Methods 0.000 description 164
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 162
- 239000000047 product Substances 0.000 description 143
- 239000007787 solid Substances 0.000 description 139
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 101
- 239000012230 colorless oil Substances 0.000 description 95
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 91
- 239000000243 solution Substances 0.000 description 85
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 66
- 230000002829 reductive effect Effects 0.000 description 66
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 59
- 239000003921 oil Substances 0.000 description 54
- 235000019198 oils Nutrition 0.000 description 54
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 150000002148 esters Chemical class 0.000 description 29
- 238000004587 chromatography analysis Methods 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- 239000012074 organic phase Substances 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
- 239000012043 crude product Substances 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 11
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 239000001530 fumaric acid Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- 238000007710 freezing Methods 0.000 description 6
- 230000008014 freezing Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 208000004454 Hyperalgesia Diseases 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 5
- 229920005990 polystyrene resin Polymers 0.000 description 5
- 210000003462 vein Anatomy 0.000 description 5
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 4
- FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 208000035154 Hyperesthesia Diseases 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 4
- 150000007514 bases Chemical class 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- 150000002576 ketones Chemical group 0.000 description 4
- 229940126601 medicinal product Drugs 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 150000002829 nitrogen Chemical group 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000003053 piperidines Chemical class 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 3
- QXYLYYZZWZQACI-UHFFFAOYSA-N 2,3,4,5-tetrafluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1F QXYLYYZZWZQACI-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 3
- 125000004747 1,1-dimethylethoxycarbonyl group Chemical group CC(C)(OC(=O)*)C 0.000 description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 2
- OHUMKYGINIODOY-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)piperazine Chemical compound C1CN(C)CCC1N1CCNCC1 OHUMKYGINIODOY-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 2
- MQHHXEFTOQSSDO-UHFFFAOYSA-N 4-formylpiperidine-1-carboxylic acid Chemical compound OC(=O)N1CCC(C=O)CC1 MQHHXEFTOQSSDO-UHFFFAOYSA-N 0.000 description 2
- FOWOXWLATUAFNQ-UHFFFAOYSA-N 4-oxopiperidine-1-carboxylic acid Chemical compound OC(=O)N1CCC(=O)CC1 FOWOXWLATUAFNQ-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 102400000967 Bradykinin Human genes 0.000 description 2
- 101800004538 Bradykinin Proteins 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0303602A FR2852958B1 (fr) | 2003-03-25 | 2003-03-25 | Nouveaux derives de benzenesulfonamides et leur utilisation en therapeutique |
| FR0304530A FR2853648B1 (fr) | 2003-04-11 | 2003-04-11 | Nouveaux derives de benzenesulfonamides et leur utilisation en therapeutique |
| PCT/FR2004/000723 WO2004087700A1 (fr) | 2003-03-25 | 2004-03-24 | Derives du benzenesulfonamide, leur procede de preparation et leur utilisation de la douleur |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05010288A true MXPA05010288A (es) | 2005-11-17 |
Family
ID=33133107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05010288A MXPA05010288A (es) | 2003-03-25 | 2004-03-24 | Derivados de bencenosulfonamida, metodo para su produccion y uso de los mismos para el tratamiento del dolor. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7538111B2 (pt) |
| EP (1) | EP1606288B1 (pt) |
| JP (1) | JP4593559B2 (pt) |
| AT (1) | ATE432930T1 (pt) |
| AU (1) | AU2004226197B2 (pt) |
| BR (1) | BRPI0408689B8 (pt) |
| CA (1) | CA2519110C (pt) |
| DE (1) | DE602004021358D1 (pt) |
| DK (1) | DK1606288T3 (pt) |
| EA (1) | EA008921B1 (pt) |
| ES (1) | ES2327338T3 (pt) |
| IL (1) | IL170630A (pt) |
| MA (1) | MA27629A1 (pt) |
| MX (1) | MXPA05010288A (pt) |
| NO (1) | NO330888B1 (pt) |
| PT (1) | PT1606288E (pt) |
| SI (1) | SI1606288T1 (pt) |
| TN (1) | TNSN05238A1 (pt) |
| UA (1) | UA83821C2 (pt) |
| WO (1) | WO2004087700A1 (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060217362A1 (en) * | 2004-12-29 | 2006-09-28 | Tung Jay S | Novel compounds useful for bradykinin B1 receptor antagonism |
| DE102006039003A1 (de) * | 2006-08-19 | 2008-02-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Verbindungen |
| WO2008046573A1 (de) * | 2006-10-16 | 2008-04-24 | Grünenthal GmbH | Substituierte sulfonamid-derivate als bradykinin 1 rezeptor modulatoren |
| DE102007034620A1 (de) * | 2007-07-25 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue B1-Antagonisten |
| MX2010001664A (es) * | 2007-08-14 | 2010-03-10 | Boehringer Ingelheim Int | Nuevos compuestos. |
| EP2025675A1 (de) * | 2007-08-14 | 2009-02-18 | Boehringer Ingelheim International GmbH | Arylsulfonamide mit analgetischer Wirkung |
| EP2229395A1 (en) | 2008-01-17 | 2010-09-22 | Grünenthal GmbH | Substituted sulfonamide derivatives |
| TW200940523A (en) * | 2008-03-17 | 2009-10-01 | Gruenenthal Gmbh | Substituted sulfonamide derivatives |
| PE20091782A1 (es) | 2008-04-08 | 2009-11-15 | Gruenenthal Chemie | Derivados de sulfonamida sustituida |
| PE20091731A1 (es) | 2008-04-08 | 2009-11-11 | Gruenenthal Chemie | Derivados de sulfonamida sustituida |
| TWI482629B (zh) * | 2008-07-01 | 2015-05-01 | Tobishi Pharmaceutical Co | 下泌尿道疾病治療劑及下泌尿道症狀改善劑 |
| US8207335B2 (en) * | 2009-02-13 | 2012-06-26 | Boehringer Ingelheim International Gmbh | Process for making certain compounds having B1 antagonistic activity |
| WO2023028056A1 (en) | 2021-08-24 | 2023-03-02 | Genentech, Inc. | 3-amino piperidyl sodium channel inhibitors |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT84170B (pt) | 1986-01-24 | 1989-03-30 | Sanofi Sa | Processo para a preparacao de derivados n alfa-substituidos das n alfa-aril-sulfonilaminoacil d-amidinofenil-alaninamidas |
| PT84171B (pt) * | 1986-01-24 | 1989-03-30 | Sanofi Sa | Processo para a preparacao de derivados das n alfa-aril-sulfonilamiminoacil-p- -amidinofenil-alaninamidas, bem como dos seus derivados de sintese e das composicoes farmaceuticas que os contem |
| WO1992016549A1 (de) | 1991-03-18 | 1992-10-01 | Pentapharm Ag | Para-substituierte phenylalanin-derivate |
| DE4206858A1 (de) | 1992-03-05 | 1993-09-09 | Behringwerke Ag | Glycopeptid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel |
| FR2701480B1 (fr) * | 1993-02-15 | 1995-05-24 | Sanofi Elf | Composés à groupe sulfamoyle et amidino, leur procédé de préparation et les compositions pharmaceutiques les contenant. |
| IL115420A0 (en) * | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
| FR2735128B1 (fr) | 1995-06-07 | 1997-07-25 | Fournier Ind & Sante | Nouveaux composes de benzenesulfonamide, leur procede de preparation et utilisation en therapeutique. |
| US5834431A (en) | 1995-09-08 | 1998-11-10 | Cortech, Inc. | Des-Arg9 -BK antagonists |
| FR2743073B1 (fr) | 1995-12-29 | 1998-02-20 | Fournier Ind & Sante | Nouveaux composes de 1-benzenesulfonylpyrrolidine, procede de preparation et utilisation en therapeutique |
| FR2743562B1 (fr) * | 1996-01-11 | 1998-04-03 | Sanofi Sa | Derives de n-(arylsulfonyl) aminoacides, leur preparation, les compositions pharmaceutiques en contenant |
| FR2751650B1 (fr) | 1996-07-24 | 1998-10-09 | Fournier Ind & Sante | Nouveaux composes de n-benzenesulfonyl-l-proline, procede de preparation et utilisation en therapeutique |
| IL128189A0 (en) * | 1996-08-23 | 1999-11-30 | Pfizer | Arylsulfonylamino hydroxamic acid derivatives |
| GB9621814D0 (en) * | 1996-10-19 | 1996-12-11 | British Biotech Pharm | Metalloproteinase inhibitors |
| FR2756562B1 (fr) | 1996-12-04 | 1999-01-08 | Fournier Ind & Sante | Nouveaux composes de n-benzenesulfonyl-l-proline, procede de preparation et utilisation en therapeutique |
| FR2766148B1 (fr) | 1997-07-16 | 1999-09-17 | Soc D Const De Materiel Metall | Chariot comportant un dispositif de refroidissement pouvant etre mis en oeuvre a l'instant choisi par l'utilisateur et procede pour apporter un mets rechauffe |
| CA2379064A1 (en) | 1999-07-15 | 2001-01-25 | Pharmacopeia, Inc. | Bradykinin b1 receptor antagonists |
| SE9903930D0 (sv) * | 1999-10-29 | 1999-10-29 | Astra Pharma Inc | Novel compounds and a novel process for their preparation |
| FR2819254B1 (fr) * | 2001-01-08 | 2003-04-18 | Fournier Lab Sa | Nouveaux composes de la n-(phenylsulfonyl) glycine, leur procede de preparation et leur utilisation pour obtenir des compostions pharmaceutiques |
| AR033879A1 (es) * | 2001-05-07 | 2004-01-07 | Smithkline Beecham Corp | Compuesto sulfonamida, composicion farmaceutica que lo comprende, su uso para preparar dicha composicion y procedimiento para la obtencion de dicho compuesto |
| WO2002099388A2 (en) | 2001-06-07 | 2002-12-12 | Merck & Co., Inc. | Benzodiazepine bradykinin antagonists |
-
2004
- 2004-03-24 JP JP2006505749A patent/JP4593559B2/ja not_active Expired - Lifetime
- 2004-03-24 EP EP04742333A patent/EP1606288B1/fr not_active Expired - Lifetime
- 2004-03-24 WO PCT/FR2004/000723 patent/WO2004087700A1/fr active Application Filing
- 2004-03-24 EA EA200501310A patent/EA008921B1/ru unknown
- 2004-03-24 CA CA2519110A patent/CA2519110C/fr not_active Expired - Lifetime
- 2004-03-24 AT AT04742333T patent/ATE432930T1/de active
- 2004-03-24 DE DE602004021358T patent/DE602004021358D1/de not_active Expired - Lifetime
- 2004-03-24 ES ES04742333T patent/ES2327338T3/es not_active Expired - Lifetime
- 2004-03-24 UA UAA200509011A patent/UA83821C2/ru unknown
- 2004-03-24 MX MXPA05010288A patent/MXPA05010288A/es active IP Right Grant
- 2004-03-24 SI SI200431203T patent/SI1606288T1/sl unknown
- 2004-03-24 DK DK04742333T patent/DK1606288T3/da active
- 2004-03-24 US US10/549,546 patent/US7538111B2/en not_active Expired - Lifetime
- 2004-03-24 PT PT04742333T patent/PT1606288E/pt unknown
- 2004-03-24 BR BRPI0408689A patent/BRPI0408689B8/pt active IP Right Grant
- 2004-03-24 AU AU2004226197A patent/AU2004226197B2/en not_active Expired
-
2005
- 2005-09-01 IL IL170630A patent/IL170630A/en active IP Right Grant
- 2005-09-06 MA MA28480A patent/MA27629A1/fr unknown
- 2005-09-20 NO NO20054361A patent/NO330888B1/no unknown
- 2005-09-23 TN TNP2005000238A patent/TNSN05238A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA200501310A1 (ru) | 2006-06-30 |
| ES2327338T3 (es) | 2009-10-28 |
| DE602004021358D1 (de) | 2009-07-16 |
| BRPI0408689B1 (pt) | 2018-09-11 |
| JP4593559B2 (ja) | 2010-12-08 |
| BRPI0408689A (pt) | 2006-03-28 |
| MA27629A1 (fr) | 2005-11-01 |
| JP2006521333A (ja) | 2006-09-21 |
| CA2519110C (fr) | 2012-09-18 |
| NO330888B1 (no) | 2011-08-08 |
| EA008921B1 (ru) | 2007-08-31 |
| SI1606288T1 (sl) | 2009-10-31 |
| EP1606288A1 (fr) | 2005-12-21 |
| ATE432930T1 (de) | 2009-06-15 |
| AU2004226197A1 (en) | 2004-10-14 |
| US20060178360A1 (en) | 2006-08-10 |
| WO2004087700A8 (fr) | 2004-11-18 |
| NO20054361L (no) | 2005-11-01 |
| EP1606288B1 (fr) | 2009-06-03 |
| US7538111B2 (en) | 2009-05-26 |
| NO20054361D0 (no) | 2005-09-20 |
| TNSN05238A1 (fr) | 2007-06-11 |
| UA83821C2 (ru) | 2008-08-26 |
| WO2004087700A1 (fr) | 2004-10-14 |
| BRPI0408689B8 (pt) | 2021-05-25 |
| PT1606288E (pt) | 2009-08-26 |
| DK1606288T3 (da) | 2009-10-05 |
| CA2519110A1 (fr) | 2004-10-14 |
| IL170630A (en) | 2012-02-29 |
| AU2004226197B2 (en) | 2009-12-03 |
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